A couple of years ago, my husband received an unexpected bonus: two extra weeks off. The only question was where to go. Chile? Albania? Mauritius? These were, of course, all my suggestions.
“South Africa”
Say, what? Big trips are my department, and South Africa wasn’t even on my current radar. I called my mother who did a Backroads cycling trip there.
“Oh, you’ll love it,” she said. “It’s incredible.”
I genuinely love the challenge of pulling off an ambitious trip, and we ended up visiting five countries! Thinking about South Africa (blog post coming soon) made me realize just how many steps go into making a vacation feel effortless.
Before becoming a travel advisor (read about me here), I worked as a production coordinator in the film industry. Part of my job was getting everyone in the crew on location so I learned to plan complicated itineraries, juggle personalities and cater to wildly different preferences. On a film set, one bad mistake could get you fired or at least make for a very long day. Honing those skills has translated surprisingly well to what I do now.
So I thought I’d share some of the things I do when planning my own trips and my clients’ trips to help ensure everything goes smoothly.
Lounges, Layovers and how to enjoy an airport
Most people don’t give the airport much thought—or, if they do, the goal is simply to get through it. In my book, your vacation starts the moment you leave the house, and those first 24 hours can make or break the trip.
My kids poke fun at my obsession with flight routings, airplane cabin configurations and subpar airport lounges—not to mention my penchant for extra-long layovers. Why risk a frantic connection when you could go shopping instead? (Hello, Heathrow. I’m talking to you.)
When we planned a trip to St. Lucia, every flight seemed to arrive at an ungodly hour. So we turned the journey into part of the vacation: we overnighted in Miami, stayed at the hotel where we got married and went out for stone crabs.
Who says you can’t have fun getting there?
Because you shouldn’t need a vacation from your vacation
Next is your arrival experience at your destination. It’s no fun to navigate a foreign place when you’re too exhausted to think so instead of struggling with Uber or taxis, I like to book a Meet & Greet Transfer. I also book (when possible) at a full-service hotel that has a pool or spa, executive lounge or on-site restaurant so there is a way to recharge and relax if your room isn’t ready.
Your Last Day Matters
Trips packed with sightseeing can leave you feeling like you need a vacation from your vacation.
Before I was a travel advisor, as the designated travel expert in the family, I planned a two-week, multi-generational trip across Peru for my family, my brother’s family and my parents (blog post coming soon).
It was ambitious to say the least, and there was some pushback from my brother telling me the itinerary was a little too adventurous for his family. He suggested ending the trip by staying a couple of days at a resort to relax.
“Uh, relax?”
At first, I thought he was nuts—you can relax at home! But as a full-time orthopedic surgeon with teenagers, he and his wife needed more than a single day of doing nothing. In the interest of family harmony, I agreed—and you know what? It was fantastic!
We each had our own casita, and I managed to squeeze in some extra activities for those of us allergic to hanging out. We took a lovely boat ride to Islas Ballestas, went sand-dune sledding, and the next day lounged by the pool. I remember how nice it was, our family gathered on the patio for an alfresco farewell dinner before heading home. It was the perfect ending to a truly memorable trip.
Now I always try to build in a little R&R at the end of each trip. I’m currently planning a two-week girls’ trip to Chile where the final two nights will be at the Ritz-Carlton Santiago, for a gloriously unproductive spa day before flying home.
The Great Transportation Dilemma
Not everyone travels with an unflappable, Boston-born husband who can drive through absolute chaos without seeming to notice. Cars coming from every direction? Motorcycles threading between lanes? Traffic laws that feel more like gentle suggestions? Just another Tuesday.
Knowing whether or not you should rent a car, take public transit, call an Uber or arrange a private transfer is huge. If you’re renting a car, should you pick it up at the airport or could you get a better deal near your hotel? (most likely yes) Does the hotel have parking, and how much will that cost? If you’re relying on public transit, which app do you need to navigate the system, and how do you buy tickets?
These are the unglamorous details I sort out for my clients so they can spend less time worrying about logistics—and more time enjoying the trip.
For clients who prefer to drive themselves, I calculate comfortable daily distances, recommend worthwhile sightseeing stops and find a fun place for lunch along the way. I also investigate tolls, local driving customs and that all-important question: does their hotel have parking?
Build a Trip Around What You Actually Love
Maybe you want to play golf in Scotland. Or ski in Argentina. Or take a cooking class in Italy. It’s fun to incorporate a special interest or hobby into a trip to truly make it personalized. I love to wander and be outside so my trips include lots of days for outdoor explorations and hikes.
You Pack the Bags; I’ll Obsess Over the Details
So, if you are too busy, or can’t figure out which deck to pick on a cruise ship or just want to have a fun, enthusiastic partner do the legwork while you sit back and enjoy your vacation, reach out! That’s what I am here for.
Lillian Martin is the Senior Travel Advisor / Travel Agent with Reece Worldwide Travel. For help planning your next vacation, please click here
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